# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'Edwin Kroke' _publ_contact_author_email EDWIN.KROKE@CHEMIE.TU-FREIBERG.DE _publ_section_title ; Sol-gel analogous aminolysis-ammonolysis of chlorosilanes to chlorine-free Si/(C)/N - materials ; loop_ _publ_author_name 'Edwin Kroke' 'Gerhard Roewer' 'Jorg Wagler' 'Conny Wiltzsch' data_cw01_r-3 _database_code_depnum_ccdc_archive 'CCDC 622385' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C9 H39 N13 Si9' _chemical_formula_sum 'C9 H39 N13 Si9' _chemical_formula_weight 582.34 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Si Si 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting trigonal _symmetry_space_group_name_H-M R-3 _symmetry_space_group_name_Hall -R3 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' 'x+2/3, y+1/3, z+1/3' '-y+2/3, x-y+1/3, z+1/3' '-x+y+2/3, -x+1/3, z+1/3' 'x+1/3, y+2/3, z+2/3' '-y+1/3, x-y+2/3, z+2/3' '-x+y+1/3, -x+2/3, z+2/3' '-x, -y, -z' 'y, -x+y, -z' 'x-y, x, -z' '-x+2/3, -y+1/3, -z+1/3' 'y+2/3, -x+y+1/3, -z+1/3' 'x-y+2/3, x+1/3, -z+1/3' '-x+1/3, -y+2/3, -z+2/3' 'y+1/3, -x+y+2/3, -z+2/3' 'x-y+1/3, x+2/3, -z+2/3' _cell_length_a 12.5915(7) _cell_length_b 12.5915(7) _cell_length_c 30.8770(14) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 4239.6(4) _cell_formula_units_Z 6 _cell_measurement_temperature 93(2) _cell_measurement_reflns_used 7399 _cell_measurement_theta_min 3.23 _cell_measurement_theta_max 29.15 _exptl_crystal_description cube _exptl_crystal_colour colorless _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.369 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1860 _exptl_absorpt_coefficient_mu 0.449 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8255 _exptl_absorpt_correction_T_max 0.9156 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 93(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 20394 _diffrn_reflns_av_R_equivalents 0.0335 _diffrn_reflns_av_sigmaI/netI 0.0149 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -39 _diffrn_reflns_limit_l_max 40 _diffrn_reflns_theta_min 1.98 _diffrn_reflns_theta_max 27.50 _reflns_number_total 2172 _reflns_number_gt 2020 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP32 (Farugia)' _computing_publication_material 'Ciftab (Sheldrick)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0275P)^2^+28.6407P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2172 _refine_ls_number_parameters 97 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0518 _refine_ls_R_factor_gt 0.0481 _refine_ls_wR_factor_ref 0.1140 _refine_ls_wR_factor_gt 0.1126 _refine_ls_goodness_of_fit_ref 1.218 _refine_ls_restrained_S_all 1.218 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Si1 Si 0.55926(8) 0.38937(7) 0.21295(2) 0.0242(2) Uani 1 1 d . . . Si2 Si 0.50510(7) 0.45868(7) 0.12034(3) 0.01980(19) Uani 1 1 d . . . Si3 Si 0.73254(7) 0.49159(7) 0.07324(2) 0.02006(19) Uani 1 1 d . . . N1 N 0.5228(3) 0.2390(2) 0.20793(9) 0.0326(6) Uani 1 1 d . . . H1 H 0.4453 0.1881 0.2017 0.039 Uiso 1 1 calc R . . N2 N 0.4846(2) 0.4283(2) 0.17449(8) 0.0274(5) Uani 1 1 d . . . H2 H 0.4227 0.4336 0.1852 0.033 Uiso 1 1 calc R . . N3 N 0.4470(2) 0.3326(2) 0.08612(9) 0.0297(6) Uani 1 1 d . . . H3 H 0.3767 0.3126 0.0736 0.036 Uiso 1 1 calc R . . N4 N 0.6606(2) 0.5350(2) 0.11104(7) 0.0198(5) Uani 1 1 d . . . H4 H 0.7067 0.6007 0.1267 0.024 Uiso 1 1 calc R . . N5 N 0.6667 0.3333 0.07392(13) 0.0221(8) Uani 1 3 d S . . C1 C 0.5117(4) 0.4176(3) 0.26655(11) 0.0476(10) Uani 1 1 d . . . H1A H 0.4221 0.3701 0.2689 0.071 Uiso 1 1 calc R . . H1B H 0.5394 0.5051 0.2696 0.071 Uiso 1 1 calc R . . H1C H 0.5483 0.3924 0.2895 0.071 Uiso 1 1 calc R . . C2 C 0.4244(3) 0.5443(3) 0.10646(13) 0.0378(8) Uani 1 1 d . . . H2A H 0.3359 0.4905 0.1102 0.057 Uiso 1 1 calc R . . H2B H 0.4420 0.5721 0.0763 0.057 Uiso 1 1 calc R . . H2C H 0.4530 0.6155 0.1256 0.057 Uiso 1 1 calc R . . C3 C 0.7196(4) 0.5454(4) 0.01854(10) 0.0415(9) Uani 1 1 d . . . H3A H 0.7700 0.6350 0.0172 0.062 Uiso 1 1 calc R . . H3B H 0.6338 0.5208 0.0128 0.062 Uiso 1 1 calc R . . H3C H 0.7482 0.5088 -0.0033 0.062 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Si1 0.0287(4) 0.0271(4) 0.0155(4) 0.0033(3) 0.0067(3) 0.0131(3) Si2 0.0159(3) 0.0147(3) 0.0297(4) 0.0006(3) -0.0037(3) 0.0083(3) Si3 0.0219(4) 0.0232(4) 0.0168(4) 0.0063(3) 0.0027(3) 0.0125(3) N1 0.0313(14) 0.0311(14) 0.0368(15) -0.0120(11) -0.0179(11) 0.0167(12) N2 0.0207(12) 0.0341(14) 0.0338(14) 0.0105(11) 0.0128(10) 0.0185(11) N3 0.0190(12) 0.0220(12) 0.0498(16) -0.0101(11) -0.0161(11) 0.0115(10) N4 0.0181(11) 0.0180(11) 0.0160(11) -0.0018(8) 0.0001(8) 0.0036(9) N5 0.0238(12) 0.0238(12) 0.0187(19) 0.000 0.000 0.0119(6) C1 0.053(2) 0.0332(18) 0.0295(17) -0.0084(14) 0.0201(16) 0.0009(16) C2 0.0296(16) 0.0219(14) 0.066(2) -0.0061(15) -0.0219(16) 0.0156(13) C3 0.073(3) 0.047(2) 0.0182(14) 0.0089(14) 0.0064(16) 0.041(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Si1 N1 1.718(3) . ? Si1 N1 1.723(3) 3_665 ? Si1 N2 1.731(3) . ? Si1 C1 1.854(3) . ? Si2 N2 1.706(3) . ? Si2 N4 1.720(2) . ? Si2 N3 1.735(3) . ? Si2 C2 1.864(3) . ? Si3 N4 1.725(2) . ? Si3 N3 1.726(3) 3_665 ? Si3 N5 1.7339(8) . ? Si3 C3 1.857(3) . ? N1 H1 0.8800 . ? N2 H2 0.8800 . ? N3 H3 0.8800 . ? N4 H4 0.8800 . ? N5 Si3 1.7339(8) 3_665 ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? C2 H2C 0.9800 . ? C3 H3A 0.9800 . ? C3 H3B 0.9800 . ? C3 H3C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Si1 N1 106.76(18) . 3_665 ? N1 Si1 N2 111.50(13) . . ? N1 Si1 N2 111.56(12) 3_665 . ? N1 Si1 C1 110.98(16) . . ? N1 Si1 C1 109.53(16) 3_665 . ? N2 Si1 C1 106.55(18) . . ? N2 Si2 N4 106.92(12) . . ? N2 Si2 N3 116.39(14) . . ? N4 Si2 N3 104.51(12) . . ? N2 Si2 C2 106.86(16) . . ? N4 Si2 C2 115.85(14) . . ? N3 Si2 C2 106.70(14) . . ? N4 Si3 N3 110.35(13) . 3_665 ? N4 Si3 N5 109.30(13) . . ? N3 Si3 N5 107.29(10) 3_665 . ? N4 Si3 C3 110.12(14) . . ? N3 Si3 C3 109.16(17) 3_665 . ? N5 Si3 C3 110.57(18) . . ? Si1 N1 Si1 131.56(17) . 2_655 ? Si1 N1 H1 114.2 . . ? Si1 N1 H1 114.2 2_655 . ? Si2 N2 Si1 133.91(14) . . ? Si2 N2 H2 113.0 . . ? Si1 N2 H2 113.0 . . ? Si3 N3 Si2 128.86(14) 2_655 . ? Si3 N3 H3 115.6 2_655 . ? Si2 N3 H3 115.6 . . ? Si2 N4 Si3 124.58(13) . . ? Si2 N4 H4 117.7 . . ? Si3 N4 H4 117.7 . . ? Si3 N5 Si3 119.987(7) 3_665 . ? Si3 N5 Si3 119.985(7) 3_665 2_655 ? Si3 N5 Si3 119.985(7) . 2_655 ? Si1 C1 H1A 109.5 . . ? Si1 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? Si1 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? Si2 C2 H2A 109.5 . . ? Si2 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? Si2 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? Si3 C3 H3A 109.5 . . ? Si3 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? Si3 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 Si1 N1 Si1 18.6(3) 3_665 . . 2_655 ? N2 Si1 N1 Si1 140.7(2) . . . 2_655 ? C1 Si1 N1 Si1 -100.7(3) . . . 2_655 ? N4 Si2 N2 Si1 -36.1(3) . . . . ? N3 Si2 N2 Si1 80.2(2) . . . . ? C2 Si2 N2 Si1 -160.7(2) . . . . ? N1 Si1 N2 Si2 -75.4(2) . . . . ? N1 Si1 N2 Si2 43.8(3) 3_665 . . . ? C1 Si1 N2 Si2 163.3(2) . . . . ? N2 Si2 N3 Si3 -78.9(2) . . . 2_655 ? N4 Si2 N3 Si3 38.8(2) . . . 2_655 ? C2 Si2 N3 Si3 162.0(2) . . . 2_655 ? N2 Si2 N4 Si3 126.77(16) . . . . ? N3 Si2 N4 Si3 2.8(2) . . . . ? C2 Si2 N4 Si3 -114.27(19) . . . . ? N3 Si3 N4 Si2 -158.55(15) 3_665 . . . ? N5 Si3 N4 Si2 -40.8(2) . . . . ? C3 Si3 N4 Si2 80.9(2) . . . . ? N4 Si3 N5 Si3 -135.0(2) . . . 3_665 ? N3 Si3 N5 Si3 -15.4(3) 3_665 . . 3_665 ? C3 Si3 N5 Si3 103.6(3) . . . 3_665 ? N4 Si3 N5 Si3 47.3(3) . . . 2_655 ? N3 Si3 N5 Si3 167.0(2) 3_665 . . 2_655 ? C3 Si3 N5 Si3 -74.1(3) . . . 2_655 ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.468 _refine_diff_density_min -0.577 _refine_diff_density_rms 0.078